16107-82-7

Upstream product

• 40288-69-5 N-(2-cyanophenyl)benzamide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 36192-63-9 2-amino-4'-methylbenzophenone 
• 100-46-9 benzylamine 
• 108-88-3 toluene 
• 6484-25-9 4-chloro-2-phenylquinazoline 
• 14338-21-7 tri-(4-methylphenyl)aluminum 
• 1315336-92-5 2-phenylquinazolin-4-yl 4-methylbenzenesulfonate 
• 103-82-2 phenylacetic acid 
• 589-18-4 4-Methylbenzyl alcohol 
• 1527-91-9 N-phenylbenzamidine 
• 104-87-0 4-methyl-benzaldehyde 
• 5720-05-8 4-methylphenylboronic acid 
• 1022-45-3 2-phenyl-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Ring-Opening Rearrangements of 2-(Benzotriazol-1-yl) Enamines and a Novel Synthesis of 2,4-Diarylquinazoline

2-(Benzotriazol-1-yl) enamines (readily available from lithiated 1-(arylmethyl) benzotriazole and nitriles) undergo facile rearrangement into 2,4-diarylquinazolines.A plausible mechanism for this novel rearrangement is proposed and supported.

Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines

The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).

Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines

A one-pot method for joining three separate components leading to an assortment of 4-arylquinazolines (27 examples) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed?-cascade reaction involving C(sp)-C(sp 2/s

TMSOTf-catalyzed synthesis of substituted quinazolines using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions

In this article, we report an efficient and mild synthetic route for the construction of substituted quinazolines from functionalized 2-aminobenzophenones with various benzaldehydes usingcat. TMSOTf and hexamethyldisilazane (HMDS) under neat, metal-free and microwave irradiation conditions in which gaseous ammonia was formedin situ. This synthetic protocol provided the desired quinazolines with a broad substrate scope in good to excellent yields. Some structures were confirmed by X-ray single-crystal diffraction analysis.

Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines

The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, ha

Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines

A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C–H activation/C–N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.

Palladium-Catalyzed Three-Component Tandem Process: One-Pot Assembly of Quinazolines

The first example of the palladium-catalyzed, three-component tandem reaction of 2-aminobenzonitriles, aldehydes, and arylboronic acids has been developed, providing a new approach for one-pot assembly of diverse quinazolines in moderate to good yields. A noteworthy feature of this method is the tolerance of bromo and iodo groups, which affords versatility for further synthetic manipulations. Preliminary mechanistic experiments indicate that this tandem process involves two possible mechanistic pathways for the formation of quinazolines via catalytic carbopalladation of the cyano group.

Heterogeneous oxidative synthesis of quinazolines over OMS-2 under ligand-free conditions

A manganese oxide octahedral molecular sieve (OMS-2) prepared using urea as an additive was found to be an efficient recyclable catalyst for the synthesis of quinazolines via oxidation/cyclization. A broad range of substituted quinazolines were obtained from alcohols and amidines in good yields under ligand-free conditions. OMS-2 was characterized by XRD, BET, ICP-AES, SEM, TEM and XPS, which indicated that the superior catalytic ability might arise from enhanced surface area and crystallinity.

General copper-catalyzed coupling of alkyl-, aryl-, and alkynylaluminum reagents with organohalides

We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic coupling partners. These reactions are not complicated by β-hydride elimination, and as a result rearranged products are not observed with secondary alkylaluminum reagents even for couplings with heteroaryl halides under "ligand-free" conditions. Radical clock experiment with a radical probe and relative reactivity study of Ph3Al with two haloarenes, 1-bromonaphthalene and 4-chlorobenzonitrile, having two different redox potentials indicates that the reaction does not involve free aryl radicals and radical anions as intermediates. These results combined with the result of the Hammett plot obtained by reacting Ph3Al with iodoarenes containing p-H, p-Me, p-F, and p-CF3 substituents, which shows a linear curve (R2 = 0.99) with a ρ value of +1.06, suggest that the current transformation follows an oxidative addition-reductive elimination pathway.

Heterogeneous Palladium-Catalyzed Hydrogen-Transfer Cyclization of Nitroacetophenones with Benzylamines: Access to C?N Bonds

The first Pd/C-catalyzed oxidative C(sp3)?H bond amination of o-nitroacetophenones with benzylamines or amino acids proceeding through C?N bond cleavage followed by C?N bond formation by a hydrogen-transfer strategy was developed. These transformations proceeded smoothly in water to afford the desired quinazolines in moderate to good yields. This protocol has a broad substrate scope and good tolerance of air, offers excellent recyclability of the catalyst, and does not need any additional oxidant, ligand, or base; the combination of all of these factors give a new and practical avenue for multiple C?N bond formation. Moreover, a hot filtration experiment indicated that heterogeneous palladium nanoparticles during the reaction are the active species.